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The solid-state structure of the title en­amino­ne, C15H17N1O7, the C adduct obtained from the reaction of 4-amino­pent-3-en-2-one with methoxy­methyl­ene Meldrum's acid, has been investigated by X-ray diffraction, and several structural features are different from the previously described structure of the corresponding N adduct. The carbonyl group of the en­amino­ne moiety of the C adduct is not coplanar with the en­amine fragment. One bifurcated intramolecular N—H...O hydrogen bond [2.688 (2) and 2.668 (2) Å] and two intermolecular C—H...O hydrogen bonds [3.339 (3) and 3.379 (3) Å] are observed. The structure packs in a linear fashion along the [100] direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804030211/kp6019sup1.cif
Contains datablocks global, IIIc

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804030211/kp6019IIIcsup2.hkl
Contains datablock IIIc

CCDC reference: 259853

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.056
  • wR factor = 0.162
  • Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



No errors found in this datablock

Computing details top

Data collection: CAD-4-PC (Enraf–Nonius, 1993); cell refinement: CAD-4-PC; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

ethyl [(Z)-2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidenemethyl)- 1-methyl-3-oxo-but-1-enylamino]acetate top
Crystal data top
C16H21NO7F(000) = 720
Mr = 339.34Dx = 1.355 Mg m3
Monoclinic, P21/cMelting point = 412–415 K
Hall symbol: -P 2ybcCu Kα radiation, λ = 1.54180 Å
a = 16.324 (2) ÅCell parameters from 25 reflections
b = 9.478 (1) Åθ = 13.1–28.7°
c = 11.062 (2) ŵ = 0.90 mm1
β = 103.69 (1)°T = 293 K
V = 1662.9 (4) Å3Prism, yellow
Z = 40.33 × 0.18 × 0.15 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.044
Radiation source: fine-focus sealed tubeθmax = 67.2°, θmin = 2.8°
Graphite monochromatorh = 019
ω–2θ scansk = 110
3072 measured reflectionsl = 1312
2978 independent reflections2 standard reflections every 129 min
2304 reflections with I > 2σ(I) intensity decay: <1.0%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.163 w = 1/[σ2(Fo2) + (0.1046P)2 + 0.187P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
2978 reflectionsΔρmax = 0.27 e Å3
230 parametersΔρmin = 0.27 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.010 (1)
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O11.21481 (9)0.13425 (17)0.81314 (15)0.0618 (4)
O21.17075 (11)0.23360 (19)0.97006 (17)0.0721 (5)
O30.97068 (10)0.31469 (18)1.04251 (16)0.0705 (5)
O40.62670 (10)0.00513 (18)0.79400 (16)0.0682 (5)
O50.57765 (9)0.12099 (17)0.93399 (15)0.0613 (4)
O60.66828 (9)0.21696 (17)1.11133 (13)0.0582 (4)
O70.80650 (9)0.21545 (18)1.14054 (13)0.0585 (4)
N11.01424 (11)0.13006 (18)0.88673 (16)0.0485 (4)
C11.15935 (13)0.1589 (2)0.8805 (2)0.0510 (5)
C21.07866 (13)0.0797 (2)0.8275 (2)0.0496 (5)
C30.93473 (12)0.0870 (2)0.86241 (17)0.0447 (5)
C40.87499 (12)0.1570 (2)0.91528 (17)0.0440 (5)
C50.79115 (12)0.1080 (2)0.88807 (18)0.0458 (5)
C60.72613 (12)0.1370 (2)0.94445 (19)0.0465 (5)
C70.64266 (13)0.0821 (2)0.8832 (2)0.0520 (5)
C80.59025 (13)0.2359 (2)1.0217 (2)0.0561 (5)
C90.73911 (12)0.1949 (2)1.06886 (18)0.0471 (5)
C100.58963 (16)0.3753 (3)0.9549 (3)0.0713 (7)
H10A0.59790.45081.01440.107*
H10B0.53640.38720.89630.107*
H10C0.63420.37630.91180.107*
C110.52173 (16)0.2241 (3)1.0912 (3)0.0770 (8)
H11A0.52740.29921.15090.115*
H11B0.52630.13501.13350.115*
H11C0.46770.23061.03360.115*
C120.89942 (13)0.2943 (2)0.97843 (18)0.0488 (5)
C130.84012 (15)0.4166 (2)0.9466 (2)0.0595 (6)
H13A0.86410.49760.99410.089*0.50
H13B0.78740.39330.96580.089*0.50
H13C0.83090.43720.85940.089*0.50
H13D0.79080.38780.88550.089*0.50
H13E0.86750.49210.91370.089*0.50
H13F0.82400.44821.02010.089*0.50
C140.91296 (14)0.0379 (2)0.7780 (2)0.0583 (6)
H14A0.91910.01340.69640.087*
H14B0.85570.06560.77340.087*
H14C0.95010.11470.81000.087*
C151.29647 (15)0.2029 (3)0.8509 (3)0.0718 (7)
H15A1.32450.17530.93490.086*
H15B1.28980.30460.84860.086*
C161.34631 (18)0.1577 (4)0.7624 (3)0.0877 (9)
H16A1.40120.20020.78480.132*
H16B1.31820.18660.67980.132*
H16C1.35200.05680.76490.132*
H1N1.028 (2)0.200 (4)0.936 (3)0.105*
H2A1.0900 (18)0.018 (4)0.844 (3)0.105*
H2B1.0627 (19)0.093 (4)0.741 (3)0.105*
H50.7706 (19)0.048 (4)0.818 (3)0.105*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0530 (8)0.0632 (9)0.0718 (10)0.0059 (7)0.0198 (7)0.0073 (8)
O20.0664 (10)0.0702 (11)0.0792 (11)0.0044 (8)0.0162 (8)0.0247 (9)
O30.0565 (9)0.0678 (10)0.0803 (11)0.0008 (8)0.0025 (8)0.0294 (9)
O40.0630 (10)0.0634 (10)0.0757 (11)0.0103 (8)0.0113 (8)0.0238 (9)
O50.0491 (8)0.0620 (9)0.0737 (10)0.0064 (7)0.0163 (7)0.0126 (8)
O60.0526 (8)0.0691 (10)0.0544 (8)0.0031 (7)0.0158 (7)0.0040 (7)
O70.0529 (8)0.0715 (10)0.0486 (8)0.0039 (7)0.0069 (7)0.0057 (7)
N10.0492 (9)0.0456 (9)0.0507 (9)0.0039 (7)0.0116 (7)0.0026 (7)
C10.0533 (11)0.0425 (10)0.0558 (12)0.0072 (8)0.0100 (9)0.0052 (9)
C20.0505 (11)0.0465 (10)0.0518 (11)0.0062 (9)0.0125 (9)0.0008 (9)
C30.0523 (11)0.0388 (9)0.0415 (9)0.0029 (8)0.0081 (8)0.0038 (8)
C40.0500 (10)0.0385 (9)0.0416 (10)0.0039 (8)0.0074 (8)0.0003 (7)
C50.0515 (11)0.0391 (10)0.0445 (10)0.0032 (8)0.0068 (8)0.0001 (7)
C60.0495 (11)0.0388 (9)0.0499 (10)0.0018 (8)0.0092 (8)0.0000 (8)
C70.0536 (11)0.0433 (10)0.0576 (11)0.0018 (9)0.0105 (9)0.0026 (9)
C80.0500 (11)0.0574 (12)0.0606 (12)0.0010 (9)0.0124 (10)0.0073 (10)
C90.0507 (11)0.0419 (10)0.0490 (10)0.0025 (8)0.0127 (9)0.0026 (8)
C100.0669 (14)0.0587 (14)0.0871 (18)0.0134 (11)0.0160 (13)0.0042 (12)
C110.0581 (14)0.095 (2)0.0835 (17)0.0045 (13)0.0278 (13)0.0140 (15)
C120.0539 (11)0.0461 (11)0.0464 (10)0.0003 (9)0.0116 (9)0.0051 (8)
C130.0745 (14)0.0394 (10)0.0636 (13)0.0039 (10)0.0146 (11)0.0010 (9)
C140.0644 (13)0.0492 (12)0.0626 (13)0.0021 (9)0.0177 (10)0.0141 (10)
C150.0557 (13)0.0682 (15)0.0916 (18)0.0107 (11)0.0175 (12)0.0069 (14)
C160.0669 (16)0.094 (2)0.110 (2)0.0112 (15)0.0381 (15)0.0024 (18)
Geometric parameters (Å, º) top
O1—C11.322 (3)C8—C111.504 (3)
O1—C151.453 (3)C8—C101.512 (3)
O2—C11.196 (3)C10—H10A0.9600
O3—C121.226 (2)C10—H10B0.9600
O4—C71.205 (3)C10—H10C0.9600
O5—C71.364 (3)C11—H11A0.9600
O5—C81.441 (3)C11—H11B0.9600
O6—C91.363 (2)C11—H11C0.9600
O6—C81.428 (3)C12—C131.498 (3)
O7—C91.210 (2)C13—H13A0.9600
N1—C31.326 (3)C13—H13B0.9600
N1—C21.445 (3)C13—H13C0.9600
N1—H1N0.85 (3)C13—H13D0.9600
C1—C21.509 (3)C13—H13E0.9600
C2—H2A0.95 (4)C13—H13F0.9600
C2—H2B0.93 (3)C14—H14A0.9600
C3—C41.415 (3)C14—H14B0.9600
C3—C141.497 (3)C14—H14C0.9600
C4—C51.409 (3)C15—C161.477 (4)
C4—C121.486 (3)C15—H15A0.9700
C5—C61.380 (3)C15—H15B0.9700
C5—H50.96 (3)C16—H16A0.9600
C6—C91.450 (3)C16—H16B0.9600
C6—C71.466 (3)C16—H16C0.9600
C1—O1—C15117.58 (18)H11A—C11—H11B109.5
C7—O5—C8118.74 (16)C8—C11—H11C109.5
C9—O6—C8118.04 (16)H11A—C11—H11C109.5
C3—N1—C2126.06 (18)H11B—C11—H11C109.5
C3—N1—H1N118 (2)O3—C12—C4121.49 (18)
C2—N1—H1N116 (2)O3—C12—C13119.08 (19)
O2—C1—O1125.3 (2)C4—C12—C13118.71 (18)
O2—C1—C2124.5 (2)C12—C13—H13A109.5
O1—C1—C2110.18 (18)C12—C13—H13B109.5
N1—C2—C1108.78 (17)H13A—C13—H13B109.5
N1—C2—H2A111.5 (19)C12—C13—H13C109.5
C1—C2—H2A107.3 (18)H13A—C13—H13C109.5
N1—C2—H2B111.0 (19)H13B—C13—H13C109.5
C1—C2—H2B109 (2)C12—C13—H13D109.5
H2A—C2—H2B109 (3)H13A—C13—H13D141.1
N1—C3—C4120.59 (18)H13B—C13—H13D56.3
N1—C3—C14116.51 (18)H13C—C13—H13D56.3
C4—C3—C14122.91 (18)C12—C13—H13E109.5
C5—C4—C3119.13 (18)H13A—C13—H13E56.3
C5—C4—C12121.87 (17)H13B—C13—H13E141.1
C3—C4—C12118.06 (17)H13C—C13—H13E56.3
C6—C5—C4130.56 (19)H13D—C13—H13E109.5
C6—C5—H5108.9 (19)C12—C13—H13F109.5
C4—C5—H5120.5 (19)H13A—C13—H13F56.3
C5—C6—C9123.31 (18)H13B—C13—H13F56.3
C5—C6—C7116.78 (18)H13C—C13—H13F141.1
C9—C6—C7118.95 (18)H13D—C13—H13F109.5
O4—C7—O5117.54 (18)H13E—C13—H13F109.5
O4—C7—C6126.2 (2)C3—C14—H14A109.5
O5—C7—C6116.25 (18)C3—C14—H14B109.5
O6—C8—O5109.52 (16)H14A—C14—H14B109.5
O6—C8—C11106.56 (19)C3—C14—H14C109.5
O5—C8—C11106.45 (19)H14A—C14—H14C109.5
O6—C8—C10110.52 (19)H14B—C14—H14C109.5
O5—C8—C10110.36 (19)O1—C15—C16106.9 (2)
C11—C8—C10113.3 (2)O1—C15—H15A110.3
O7—C9—O6117.60 (18)C16—C15—H15A110.3
O7—C9—C6126.08 (18)O1—C15—H15B110.3
O6—C9—C6116.10 (17)C16—C15—H15B110.3
C8—C10—H10A109.5H15A—C15—H15B108.6
C8—C10—H10B109.5C15—C16—H16A109.5
H10A—C10—H10B109.5C15—C16—H16B109.5
C8—C10—H10C109.5H16A—C16—H16B109.5
H10A—C10—H10C109.5C15—C16—H16C109.5
H10B—C10—H10C109.5H16A—C16—H16C109.5
C8—C11—H11A109.5H16B—C16—H16C109.5
C8—C11—H11B109.5
C15—O1—C1—O20.2 (3)C5—C6—C7—O5174.84 (18)
C15—O1—C1—C2179.80 (19)C9—C6—C7—O516.0 (3)
C3—N1—C2—C1178.66 (18)C9—O6—C8—O552.4 (2)
O2—C1—C2—N110.9 (3)C9—O6—C8—C11167.15 (19)
O1—C1—C2—N1168.64 (16)C9—O6—C8—C1069.4 (2)
C2—N1—C3—C4171.90 (18)C7—O5—C8—O647.2 (3)
C2—N1—C3—C148.4 (3)C7—O5—C8—C11162.0 (2)
N1—C3—C4—C5179.64 (17)C7—O5—C8—C1074.7 (2)
C14—C3—C4—C50.0 (3)C8—O6—C9—O7161.10 (19)
N1—C3—C4—C1211.3 (3)C8—O6—C9—C624.0 (3)
C14—C3—C4—C12169.07 (18)C5—C6—C9—O75.4 (3)
C3—C4—C5—C6165.4 (2)C7—C6—C9—O7163.0 (2)
C12—C4—C5—C625.9 (3)C5—C6—C9—O6179.76 (18)
C4—C5—C6—C918.9 (3)C7—C6—C9—O611.4 (3)
C4—C5—C6—C7172.49 (19)C5—C4—C12—O3152.2 (2)
C8—O5—C7—O4166.4 (2)C3—C4—C12—O339.0 (3)
C8—O5—C7—C614.5 (3)C5—C4—C12—C1337.6 (3)
C5—C6—C7—O46.2 (3)C3—C4—C12—C13131.2 (2)
C9—C6—C7—O4163.0 (2)C1—O1—C15—C16179.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O20.85 (3)2.29 (3)2.688 (2)109 (3)
N1—H1N···O30.85 (3)1.99 (3)2.668 (2)135 (3)
C5—H5···O40.96 (3)2.34 (3)2.814 (3)110 (2)
C2—H2A···O7i0.95 (4)2.50 (3)3.339 (3)147 (3)
C2—H2B···O3ii0.93 (3)2.51 (3)3.379 (3)155 (3)
Symmetry codes: (i) x+2, y, z+2; (ii) x, y+1/2, z1/2.
 

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